YYZ - SXM

$123 Find Cheap Flights from Toronto to Simpson Bay - Compare and Save

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Everything you should know

Cheapest round-trip
$236
Typical prices: $394-$614
WestJet
Fri 10/26Wed 10/31
YYZ - SXM • Non-stop
Cheapest one-way
$123
Typical prices: $189-$294
WestJet
Thu 9/27
YYZ - SXM • Non-stop
Nonstop flights
You can fly direct with WestJet, Air Canada and Air Transat. Average duration is 4h 53m
Direct flights
+1
Direct flights
+1
Avoid delays
Most punctual • 85% on-time
Best time • Fewest delays
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 12 weeks in advance save around 26% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 23% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $289 (round-trip)
Shortest trip • 8h 11m (one-way)
Insights
Insights
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We hope you love your trip to Simpson Bay!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Toronto to Simpson Bay (YYZ-SXM)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Toronto to Simpson Bay

Mon, Oct 26 - Sat, Oct 31
WestJet Logo
9:30 am - 2:25 pmYYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
4h 55mnonstop
WestJet Logo
1:30 pm - 6:55 pmSXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
5h 25mnonstop
$236WestJet
Mon, Nov 2 - Sat, Nov 7
Multiple Airlines Logo
9:30 am - 3:25 pmYYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
4h 55mnonstop
Multiple Airlines Logo
1:25 pm - 5:50 pmSXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
5h 25mnonstop
$267Multiple Airlines
Sun, Oct 25 - Sun, Nov 1
Air Canada Logo
9:50 am - 2:45 pmYYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
4h 55mnonstop
Air Canada Logo
4:45 pm - 9:05 pmSXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
5h 20mnonstop
$270Air Canada
Mon, Oct 26 - Mon, Nov 2
Air Canada Logo
9:50 am - 2:45 pmYYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
4h 55mnonstop
Air Canada Logo
4:45 pm - 9:05 pmSXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
5h 20mnonstop
$270Air Canada
Tue, Nov 3 - Sun, Nov 8
WestJet Logo
9:30 am - 3:25 pmYYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
4h 55mnonstop
WestJet Logo
4:20 pm - 8:45 pmSXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
5h 25mnonstop
$270WestJet
Sat, Nov 28 - Sat, Dec 5
Air Transat Logo
6:30 am - 12:15 pmYYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
4h 45mnonstop
Air Transat Logo
1:05 pm - 8:15 amSXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
20h 10m1 stop Montreal Pierre Elliott Trudeau Intl
$271Air Transat
Sat, Jan 23 - Wed, Feb 3
United Airlines Logo
8:40 pm - 3:48 pmYYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
18h 08m1 stop Newark
United Airlines Logo
2:52 pm - 2:11 pmSXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
24h 19m2 stops Newark Washington, D.C. Dulles Intl
$274United Airlines
Tue, Nov 10 - Sat, Nov 14
Air Transat Logo
11:10 pm - 11:55 amYYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
11h 45m1 stop Montreal Pierre Elliott Trudeau Intl
Air Transat Logo
1:25 pm - 5:50 pmSXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
5h 25mnonstop
$277Air Transat
Sun, Oct 25 - Sun, Nov 1
American Airlines Logo
6:00 am - 3:39 pmYYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
9h 39m1 stop Miami
American Airlines Logo
3:41 pm - 10:36 pmSXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
7h 55m1 stop Charlotte Douglas
$324American Airlines
Mon, Oct 26 - Mon, Nov 2
American Airlines Logo
7:24 pm - 3:39 pmYYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
20h 15m2 stops Charlotte Douglas Miami
American Airlines Logo
2:26 pm - 10:36 pmSXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
9h 10m1 stop Charlotte Douglas
$339American Airlines
Booking Insights

Price, demand and travel trends for Toronto Pearson Intl Airport to Simpson Bay flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Toronto Pearson Intl Airport to Simpson Bay with more confidence.

How much is a round-trip flight from Toronto Pearson Intl Airport to Simpson Bay?

Round-trip flights from Toronto Pearson Intl Airport to Simpson Bay start at $236. Prices are below average for this route right now, with typical round-trip fares ranging from $394 to $614. The lowest price found in the past 5 days was $236 on WestJet.

What's the cheapest day of the week to fly from Toronto Pearson Intl Airport to Simpson Bay?

Tuesday is the cheapest day of the week to fly from Toronto Pearson Intl Airport to Simpson Bay, it is 9% cheaper than the average day. Saturday is the most expensive day with flight prices 15% higher than average. Based on deals found by KAYAK users in the last 12 months.

What is the cheapest month to fly from Toronto Pearson Intl Airport to Simpson Bay?

  • June is the cheapest month to fly from Toronto Pearson Intl Airport to Simpson Bay at $377 round-trip.
  • December ($564) and February ($544) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 49% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are prices from Toronto Pearson Intl Airport to Simpson Bay the cheapest?

Flights from Toronto Pearson Intl Airport to Simpson Bay are cheapest 12 weeks before departure. Booking in this window typically costs about 26% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Expert advice

Expert advice for your flight from Toronto to Simpson Bay

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on WestJet and Air Canada

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

John Walton

John Walton

Expert on Air Transat

Independent aviation journalist John Walton took his first flight at eight weeks old and hasn’t stopped travelling since. A world-renowned expert in airlines and the passenger experience, he writes in depth on aviation, is a resident expert on travel in Japan and France, and offers a uniquely queer perspective on travelling the world.

Key details for Toronto Pearson Intl Airport to Simpson Bay flights

Low season

September

Cheapest flight

$123
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from Toronto Pearson Intl Airport to Simpson Bay

When to book flights from Toronto to Simpson Bay

Are your dates flexible? Find out the best times to travel from Toronto to Simpson Bay based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Toronto Pearson Intl Airport to Simpson Bay flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • Which airlines offer extra legroom and free seat selection on Toronto Pearson Intl Airport to Simpson Bay flights?

    Among airlines operating Toronto Pearson Intl Airport to Simpson Bay flights:

    • WestJet: offers extra legroom; offers free seat selection
    • Air Canada: offers extra legroom; offers free seat selection
    • Air Transat: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • What airlines are available from Toronto Pearson Intl Airport to Simpson Bay?

    3 airlines operate flights between Toronto Pearson Intl Airport and Simpson Bay. The airlines offering nonstop flights on this route include:

    • WestJet
    • Air Canada
    • Air Transat

  • Which airports can I use when flying from Toronto Pearson Intl Airport to Simpson Bay?

    Flights from Toronto Pearson Intl Airport to Simpson Bay usually depart from Toronto Pearson Intl (YYZ) and arrive at Simpson Bay Princess Juliana (SXM).

  • Which airlines include bags at no extra cost on Toronto Pearson Intl Airport to Simpson Bay flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • WestJet: a cabin bag and a checked bag in Economy Class
    • Air Canada: a cabin bag and a checked bag in Economy Class
    • Air Transat: a cabin bag and a checked bag in Economy Class

    Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

  • What cabin classes can I book on flights from Toronto Pearson Intl Airport to Simpson Bay?

    Three cabin classes are available on flights from Toronto Pearson Intl Airport to Simpson Bay:

    • Economy Class
    • Premium Economy Class
    • Business Class

  • How much can I save by taking a layover when flying from Toronto Pearson Intl Airport to Simpson Bay?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $289 round-trip via Chicago O'Hare Intl (ORD), compared to $484 for nonstop.

  • What is the standard checked-bag allowance on flights from Toronto Pearson Intl Airport to Simpson Bay?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $30–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Toronto Pearson Intl Airport to Simpson Bay?

    The Boeing 737 MAX 8 family is used most often on this route, operated mainly by WestJet and Air Canada. Other aircraft seen on the route include Airbus A321neo variants.

  • Which airports do connecting flights from Toronto Pearson Intl Airport to Simpson Bay pass through?

    One-stop flights from Toronto Pearson Intl Airport to Simpson Bay most commonly connect through:

    • Montreal Pierre Elliott Trudeau Intl (YUL) - 20% of one-stop connections
    • Atlanta Hartsfield-Jackson (ATL) - 18% of one-stop connections
    • Charlotte Douglas (CLT) - 18% of one-stop connections
    • Miami (MIA) - 13% of one-stop connections

    Montreal Pierre Elliott Trudeau Intl (YUL) handles the largest share of one-stop connections on this route.

  • Can I save money by using flexible dates for flights from Toronto Pearson Intl Airport to Simpson Bay?

    Yes. Being flexible with your travel dates can save you up to 22% on the Toronto Pearson Intl Airport to Simpson Bay route. Tuesday is the cheapest departure day at $445 round-trip on average, while Saturday is the most expensive at $565, a difference of $120. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • At what point is a flight considered delayed from Toronto Pearson Intl Airport to Simpson Bay?

    A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Toronto Pearson Intl Airport to Simpson Bay route, 28% of flights were delayed in the past 3 months, with delays averaging 1 hour 54 minutes.

  • How are flight departures from Toronto Pearson Intl Airport to Simpson Bay spread across the day?

    Morning is the busiest departure period on Toronto Pearson Intl Airport to Simpson Bay flights, with 100% of flights leaving in that window. Afternoon departures account for 0%, evening flights for 0%, and night flights for 0%.

  • What are the earliest and latest flights from Toronto Pearson Intl Airport to Simpson Bay?

    These are the earliest and latest flight times available from Toronto Pearson Intl Airport to Simpson Bay:

    • Earliest: departs at 6:30 am and lands at 11:23 am
    • Latest: departs at 12:20 pm and lands at 5:13 pm.

    The flight takes about 4h 53m.

  • How expensive are last-minute Toronto Pearson Intl Airport to Simpson Bay flights?

    Last-minute fares on this route - booked within 2 weeks of departure - run 9% above the route average of $489. Book 12 weeks before departure for the lowest fares.

  • How long is a flight from Toronto Pearson Intl Airport to Simpson Bay?

    A nonstop flight from Toronto Pearson Intl Airport to Simpson Bay takes 4h 53m, covering 2,014 miles.

  • Do I need a passport to fly from Toronto Pearson Intl Airport to Simpson Bay?

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • How are flight prices from Toronto Pearson Intl Airport to Simpson Bay looking right now?

    One-way fares from Toronto Pearson Intl Airport to Simpson Bay are currently higher than usual. Average one-way flight prices are about $267, which is 12% above the typical average for this route.

  • How does Air Transat’s on-time performance compare to other airlines on Toronto Pearson Intl Airport to Simpson Bay flights?

    Air Transat is slightly above the route average for timely arrivals, while WestJet has a lower on-time arrival rate. On-time arrival rates on Toronto Pearson Intl Airport to Simpson Bay flights are:

    • Air Transat: 85% on time
    • WestJet: 78% on time
    • Air Canada: 59% on time

    Overall, flights on this route are on time 72% of the time on average.

  • How do delay rates compare for morning and evening flights from Toronto Pearson Intl Airport to Simpson Bay?

    Afternoon flights have the fewest delays on this route. Delays tend to pile up throughout the day as one late flight pushes the next, so earlier departures are usually more reliable.

  • How much time can I save by choosing a different layover airport from Toronto Pearson Intl Airport to Simpson Bay?

    Flying via Atlanta Hartsfield-Jackson (ATL) gives the shortest average 1-stop total travel time at 8h 11m, compared with 8h 14m via Charlotte Douglas (CLT) and 8h 15m via Newark (EWR).

  • What car rental options are available at Simpson Bay Princess Juliana Airport (SXM)?

    Simpson Bay Princess Juliana Airport (SXM) hosts 5 major car rental companies, with daily rates starting from around $2 for economy cars. Top options include:
    • Ace
    • Right Cars
    • Europcar
    • Budget
    • Alamo

  • How much should I expect to pay for a Toronto Pearson Intl Airport to Simpson Bay flight?

    Round-trip flights from Toronto Pearson Intl Airport to Simpson Bay range from $394 to $614, with an average of $489 over the past 12 months. Anything below $394 counts as a good deal.

  • Which airlines offer Wi-Fi on Toronto Pearson Intl Airport to Simpson Bay flights?

    Two airlines offer in-flight Wi-Fi on Toronto Pearson Intl Airport to Simpson Bay flights:

    • • WestJet
    • • Air Canada

    Pricing varies by airline and fare class. Some plans are included with the ticket or loyalty program; others are paid add-ons priced by flight length.

Your guide to booking Toronto Pearson Intl Airport to Simpson Bay flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Tuesday departure instead of Saturday. On this route, Tuesday flights average $445 - about $120 less than Saturday (21% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 12 weeks before you fly. On this route, that window historically saves about 26% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Toronto Pearson Intl Airport to Simpson Bay trip for June. Fares historically average $377 round-trip in that month - typically $187 less than the most expensive month, which is December (based on the last 12 months).
  • If arriving on time is high on your priority list, Air Transat is the strongest pick on this route. 85% of Air Transat flights from Toronto Pearson Intl Airport to Simpson Bay arrived on time in the past 3 months, slightly above the route's average on-time arrival rate of 72%. When flights on this route do arrive late, the average delay is 1 hour 54 minutes, so choosing a carrier with strong on-time performance can make a difference on tight schedules.
  • If you have the time, taking a 1-stop flight through Chicago O'Hare Intl Airport (ORD) can be cheaper than flying direct. The cheapest layover option averages $289 round-trip on this route - about $195 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Simpson Bay Princess Juliana Airport.
    - Hilton Vacation Club Flamingo Beach St. Maarten
    - Simpson Bay Resort Marina & Spa
    - The Atrium Beach Resort and Spa Sint Maarten, an Ascend Collection Hotel

Prefer to fly direct from Toronto to Simpson Bay?

 
Find which airlines fly direct from Toronto Pearson Intl Airport to Simpson Bay Princess Juliana Airport, which days they fly and book direct flights.

Direct departures

Toronto Pearson Intl to Simpson Bay Princess Juliana

Monday

Air Canada,WestJet

Air Canada,WestJet

Tuesday

WestJet

WestJet

Thursday

Air Canada,WestJet

Air Canada,WestJet

Friday

Air Canada,WestJet

Air Canada,WestJet

Saturday

Air Canada,Air Transat,WestJet

Air Canada,Air Transat, +1 more

Sunday

Air Canada,WestJet

Air Canada,WestJet

See more direct flights

Direct returns

Simpson Bay Princess Juliana to Toronto Pearson Intl

Monday

Air Canada,WestJet

Air Canada,WestJet

Tuesday

WestJet

WestJet

Thursday

Air Canada,WestJet

Air Canada,WestJet

Friday

Air Canada,WestJet

Air Canada,WestJet

Saturday

Air Canada,Air Transat,WestJet

Air Canada,Air Transat, +1 more

Sunday

Air Canada,WestJet

Air Canada,WestJet

See more direct flights

More options for your flight from Toronto to Simpson Bay

Complete your trip to Simpson Bay with a hotel stay or car rental